We describe a Pd-catalyzed site-selective functionalization of unactivated aliphatic C-H bonds, providing chemically differentiated 1,2-diols from monoalcohol derivatives.  The oxime was employed as both a directing group (DG) and an alcohol surrogate for this transformation. As demonstrated in a range of substrates, the C-H bonds � to the oxime group are selectively oxidized. Besides activation of the methyl groups, methylene groups (CH2) in cyclic substrates and methine groups (CH) at bridge-head positions can also be functionalized . In addition, an intriguing oxidative skeleton rearrangement was observed using the menthol-derived substrate. The use of exo-directing groups in C-H activation, as illustrated in this work, would potentially open doors for the discovery of new transformations and new cleavable DGs.

Catalytic functionalization of unactivated sp<sup>3</sup> C�H bonds via exo-directing groups: Synthesis of chemically differentiated 1,2-diols

247th National Meeting (2014)

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Catalytic functionalization of unactivated sp3 C�H bonds via exo-directing groups: Synthesis of chemically differentiated 1,2-diols

Catalytic functionalization of unactivated sp³ C�H bonds via exo-directing groups: Synthesis of chemically differentiated 1,2-diols